(2S)-1-氨基-3-(1-哌啶基)-2-丙醇 | 558479-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (2S)-1-氨基-3-(1-哌啶基)-2-丙醇
• 英文名称: (S)-1-amino-3-(piperidin-1-yl)propan-2-ol
• 英文别名: (S)-1-Amino-3-piperidin-1-ylpropan-2-ol；(2S)-1-amino-3-piperidin-1-ylpropan-2-ol
• CAS: 558479-07-5
• 化学式: C₈H₁₈N₂O
• 分子量: 158.244
• InChiKey: VOQTZJYNVJFIJW-QMMMGPOBSA-N

物化性质

• 沸点：
  268.3±7.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-1-氨基-3-(1-哌啶基)-2-丙醇 在 N-甲基吗啉 、 N-甲基吡咯烷酮 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 MS4369
  参考文献：
  名称：

  Discovery of First-in-Class Protein Arginine Methyltransferase 5 (PRMT5) Degraders

  摘要：

  The aberrant expression of protein arginine methyltransferase 5 (PRMT5) has been associated with multiple cancers. Using the proteolysis targeting chimera technology, we discovered a first-in-class PRMT5 degrader 15 (MS4322). Here, we report the design, synthesis, and characterization of compound 15 and two structurally similar controls 17 (MS4370) and 21 (MS4369), with impaired binding to the von Hippel-Lindau E3 ligase and PRMT5, respectively. Compound 15, but not 17 and 21, effectively reduced the PRMT5 protein level in MCF-7 cells. Our mechanism studies indicate that compound 15 degraded PRMT5 in an E3 ligase- and proteasome-dependent manner. Compound 15 also effectively reduced the PRMT5 protein level and inhibited growth in multiple cancer cell lines. Moreover, compound 15 was highly selective for PRMT5 in a global proteomic study and exhibited good plasma exposure in mice. Collectively, compound 15 and its two controls 17 and 21 are valuable chemical tools for exploring the PRMT5 functions in health and disease.

  DOI：

  10.1021/acs.jmedchem.0c01111
• 作为产物：
  描述：

  (R)-1-azido-3-piperidin-1-yl-propan-2-ol 在 10 % Pd(OH)2/C 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 2.0h， 生成 (2S)-1-氨基-3-(1-哌啶基)-2-丙醇
  参考文献：
  名称：

  [EN] GLYT1 TRANSPORTER INHIBITORS
  [FR] INHIBITEURS DU TRANSPORTEUR GLYT1

  摘要：

  该发明提供了化合物的结构式(I)：或其盐、溶剂合物或生理功能衍生物，其中R1至R10如规范中定义，并且这些化合物的用途。这些化合物抑制GlyT1转运体，在治疗某些神经系统和神经精神疾病，包括精神分裂症方面具有用处。

  公开号：

  WO2005049023A1

文献信息

• [EN] BH4 ANTAGONISTS AND METHODS RELATED THERETO<br/>[FR] ANTAGONISTES DE BH4 ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：UNIV EMORY

  公开号：WO2015171589A1

  公开（公告）日：2015-11-12

  The disclosure relates to BH4 inhibitors and therapeutic uses relates thereto. In certain embodiments, the disclosure relates to methods of treating or preventing cancer, such as lung cancer, comprising administering therapeutically effective amount of a pharmaceutical composition comprising a compound disclosed herein or pharmaceutically acceptable salt to a subject in need thereof.

  该公开涉及BH4抑制剂及其治疗用途。在某些实施方式中，该公开涉及治疗或预防癌症的方法，例如肺癌，包括向需要的受试者施用本公开的化合物或药学上可接受的盐组成的药物组合物的治疗有效量。
• Gly1 transporter inhibitors and uses thereof in treatment of neurological and neuropsychiatric disorders
  申请人：Bloomfield Jonathon Nic

  公开号：US20050267152A1

  公开（公告）日：2005-12-01

  The present invention relates to glycine transporter inhibiting compounds of formula (I): for treating disorders mediated by GlyT1, wherein R 1 —R 9 are as in the description.

  本发明涉及公式（I）的甘氨酸转运抑制化合物，用于治疗由GlyT1介导的疾病，其中R1-R9如描述。
• Quinolin-4-yl derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1088818A1

  公开（公告）日：2001-04-04

  The invention relates to compounds of formula wherein R1is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, nitro, cyano, lower alkyl-amino, di-lower alkyl-amino or halogen; R2is phenyl, optionally substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl, amino, lower alkyl-amino or di-lower alkyl-amino 2,3 -dihydro-benzofuran-5-yl, chroman-6-yl, naphthalen-2-yl, indan-5-yl, lower alkenyl-phenyl, 5,6,7,8-tetrahydro-naphthalenyl, 2,3-dihydro-isoindol-2-yl, 1,2,3,4-tetrahydro-naphthalenyl, benzofuran-2-yl, benzo[b]thiophen-2-yl, lower alkyl-phenyl, 3,4-dihydro-1H-isoquinolin-2-yl or thiophen-3-yl; R3 and R4are independently from each other hydrogen or lower alkyl; R5is hydrogen, lower alkyl, -CH2OH or -CH2NR6R7; R6 and R7are independently from each other hydrogen, lower alkyl, - (CH2)n-phenyl, cycloalkyl, -(CH2)m-morpholinyl or form together with the N-atom a saturated ring with 4-6 C-atoms; nis 0-3; mis 2 or 3; Xis -NR8- or -O-; or X and R5are together >N(CH2)2-; or X and R3are together >N(CH2)3-; and R8is hydrogen or lower alkyl; and to pharmaceutically acceptable acid addition salts thereof, with the exception of the following compounds (6-chloro-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol; (6-methyl-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol; (6-methoxy-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol; and (8-methoxy-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol, which may be used for the treatment of diseases, which relate to the NMDA receptor specific blockers.

  本发明涉及如下式的化合物 式中 R1为氢、低级烷基、低级烷氧基、羟基、氨基、硝基、氰基、低级烷基氨基、二低级烷基氨基或卤素； R2是苯基，可选择被低级烷基、低级烷氧基、卤素、三氟甲基、氨基、低级烷基氨基或二低级烷基氨基取代 2,3-二氢-苯并呋喃-5-基、色原-6-基、萘-2-基、茚-5-基、低级烯基-苯基、5,6,7,8-四氢-萘基、2,3-二氢-异吲哚-2-基、1,2,3,4-四氢-萘基、苯并呋喃-2-基、苯并[b]噻吩-2-基、低级烷基-苯基、3,4-二氢-1H-异喹啉-2-基或噻吩-3-基； R3 和 R4 互不独立地为氢或低级烷基； R5 为氢、低级烷基、-CH2OH 或 -CH2NR6R7； R6 和 R7 各自独立地为氢、低级烷基、-(CH2)n-苯基、环烷基、-(CH2)m-吗啉基，或与 N 原子一起形成具有 4-6 个 C 原子的饱和环； n 为 0-3； 错 2 或 3； X是-NR8-或-O-；或 X和R5共同>N(CH2)2-；或 X 和 R3 共同 >N(CH2)3-；以及 R8 为氢或低级烷基； 及其药学上可接受的酸加成盐，但以下化合物除外 (6-氯-2-苯基-4-喹啉基)-(+)-2-氨基丁醇； (6-甲基-2-苯基-4-喹啉基)-(+)-2-氨基丁醇； (6-甲氧基-2-苯基-4-喹啉基)-(+)-2-氨基丁醇；和 (8-甲氧基-2-苯基-4-喹啉基)-(+)-2-氨基丁醇，可用于治疗与 NMDA 受体特异性阻断剂有关的疾病。
• 1,3-Diaminopropan-2-ol Sulfonamides as potent and selective inhibitors of the glycine transporter type 1
  作者：Shahzad S. Rahman、Steven Coulton、Hugh J. Herdon、Graham F. Joiner、Jian Jin、Roderick A. Porter

  DOI：10.1016/j.bmcl.2006.12.063

  日期：2007.3

  High throughput screening led to the discovery of a novel series of 1,3-diaminopropan-2-ol sulfonarnides as selective GlyT-1 inhibitors. Structure-activity relationships of this novel series and optimisation of the initial hit that led to the identification of (2), a potent and selective GlyT-1 inhibitor, are also presented. (c) 2007 Elsevier Ltd. All rights reserved.
• GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1455777A1

  公开（公告）日：2004-09-15